This invention relates to polyalkyl-substituted oxocycloheptane derivatives defined according to the generic structure: ##STR3## wherein one of the dashed lines is a carbon-carbon double bond and the other of the dashed lines is a carbon-carcon single bond; or both dashed lines are carbon-carbon single bonds; wherein R.sub.1 and R.sub.2 represents hydrogen or lower alkyl with the proviso that when the dashed line at the 4-5 position is a double bond, R.sub.2 is hydrogen and when the dashed line at the 3-4 position is a double bond, R.sub.1 is hydrogen; wherein R.sub.4 represents C.sub.1 -C.sub.4 lower alkyl; and wherein Y represents chloro or bromo, perfumery uses thereof and processes for preparing same.
Inexpensive chemical compositions of matter which can provide fruity, fresh, minty, earthy, camphoraceous, sweaty, animalic, woody, patchouli-like, rooty, seedy, piney, cedarwood-like, herbaceous, dried fruit and tobacco-like aromas with fruity, dried fruit, rose, orris-like and pennyroyal-like topnotes and with fruity and ionone-like undertones are highly desirable in the art of perfumery. Many of the natural materials which provide such fragrance nuances and contribute such desired nuances to perfumery compositions as well as perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions and fabric softener articles as well as perfumed polymers are high in cost, vary in quality from one batch to another and/or are generally subject to the usual variations of natural products.
There is, accordingly, a continuing effort to find synthetic materials which will replace, enhance or augment the esential fragrance notes provided by natural essential oils or compositions thereof. Unfortunately, many of the synthetic materials either have the desired nuances only to a relatively small degree, or else contribute undesirable or unwanted odor to the compositions. The search for materials which can provide a more refined rose aroma, for example, or a more refined musky/animalic aroma, for example, has been difficult and relatively costly in the areas of both natural products and synthetic products.
Provision of the polyalkyl-substituted oxocycloheptane derivatives of our invention is considered to substantially provide solutions for the aforementioned problems.
Oxocycloheptane derivatives which are polyalkyl substituted are known for use in perfumery. However, the specific polyalkyl-substituted oxocycloheptane derivatives of our invention are novel in the form prepared herein and the processes for using same are novel.
Thus, the process described in Example V of U.K. Patent Specification No. 1,159,188 Published on July 23, 1969 (describing 3,3-dimethyl acetyl cyclohexane as a perfume ingredient having a strong minty, herbaceous odor) actually produces a mixture which also contains the compound having the structure: ##STR4## as determined by Hall and Lala, "Cyclization of Dimethyl-1,6-Octadienes, J. Org. Chem. 37, 920 (1972).
Chemical Abstracts, Volume 105, No. 227080a (Abstract of Japan Kokai 61/106532 Published on May 24, 1986) discloses the perfumery use of the compound having the structure: ##STR5##
Japan Kokai No. J61/218543 Published on Sept. 29, 1986 discloses the perfumery use of the compound having the structure: ##STR6##
Japan Kokai No. 61/218543 also discloses the perfumery use of the compound having the structure: ##STR7## as having a woody and mint aroma. Japan Kokai No. J61/218543 is abstracted at Chemical Abstracts, Volume 106, 120103q (1987).
European Published Patent Application No. 193008 Published on Sept. 3, 1986 (abstracted at Chemical Abstracts, Volume
105, No. 225873y) discloses the perfumery use of the compounds having structures: ##STR8## wherein R represents alkyl.
Although the compound having the structure: ##STR9## is disclosed as incidentally made in admixture in U.S. Pat. No. 3,869,411, at column 1, the substantially pure form of the compound: ##STR10## has never been produced and has unobvious, unexpected and advantageous properties in the field of perfumery. Furthermore, none of the other compounds of the genus of polyalkyl-substituted oxocycloheptane derivatives of our invention has been described in the prior art. The compositions of matter of our invention have unexpected, unobvious and advantageous properties when compared with other oxocycloheptanes, which are polyalkyl-substituted of the prior art.